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Synlett 2001; 2001(7): 1140-1142
DOI: 10.1055/s-2001-15166
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Lewis Acid-Catalyzed Allylation Reactions of Acylhydrazones with Tetraallyltin in Aqueous Media

Shū Kobayashi* , Tomoaki Hamada, Kei Manabe
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax + 81-3-56 84-06 34; E-mail: skobayas@mol.f.u-tokyo.ac.jp
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Publication Date:
31 December 2001 (online)

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Allylation reactions of various benzoylhydrazones with tetraallyltin were found to proceed smoothly in the presence of scandium triflate as a Lewis acid catalyst at ambient temperature in aqueous media, to afford the corresponding homoallylic amine derivatives in high yields. Three-component reactions of aldehydes, benzoylhydrazine, and tetraallyltin were also catalyzed by scandium triflate in the same media. Furthermore, a simple procedure to prepare oxazolidinone derivatives utilizing these reactions was developed.

hydrazone - Lewis acid - allylation - aqueous media - scandium triflate